Highfield-Cascade
Trail Running Calendar near Highfield-Cascade 2026-2027
Explore the top trail runs near Highfield-Cascade for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A trail 5K in Gettysburg on August 15, 2026, with a race shirt option for early registrants and an event bottle opener medal. Brewfest options and tours of the Daniel Lady Farm House and Barn are available the same day.
A community trail festival at Furnace Run Park in Shippensburg on August 29, 2026, featuring a one loop 5 kilometer race and a 1 mile event with chip timing and varied trail surfaces. Proceeds benefit Friends of Shippensburg Community Parks.
A 3.8 mile running event at Pen Mar Park that climbs about 1.8 miles to High Rock Overlook and returns to the park. Registered finishers receive an official High Rock Mountain t-shirt and there are early and race day fee options.
September 2026
A 5K cross country festival on September 15, 2026 at Franklin County Fair Grounds, with proceeds benefiting Shalom Christian Academy.
An in-person event on September 26, 2026 in Brunswick, MD featuring a trail-based 5K and timed 3-hour and 6-hour challenges on a 5 mile loop. Proceeds support Brunswick High School Track and Field equipment.
October 2026
A community trail festival in Shippensburg offering a half marathon, 5k, hike, 25 mile bike ride and a free 1 mile fun run for kids, with proceeds supporting the Cumberland Valley Rails to Trails Council.
Experience a unique trail event at Milkhouse Brewery in Mount Airy featuring a 5 mile race and timed ultra challenges. Complete as many loops as possible over four or eight hours on this scenic farm course.
The Annual Boulder Dash at Pinesburg Quarry in Williamsport, MD on October 17, 2026 offers three distances : 5 miles, 5K and 1 mile, and the quarry will be closed during the event for safety.
November 2026
Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.
February 2027
A 50 km trail run at Hashawha Environmental Center in Westminster MD, featuring varied single-track, open fields, stream crossings and 5 aid stations. Entry for 2027 uses a lottery opening January 1, with indoor facilities and hot post-race food.
April 2027
A cross country 5K at Red Shedman Farm Brewery on the Linganore Winecellars grounds, with a technical quarter zip and one pour for finishers and on-site picnic and tasting options.
A 100 mile race along the C&O Canal towpath near Knoxville MD with a 40 mile loop plus two 30 mile loops, multiple aid stations, and a Camp Manidokan start.
May 2027
June 2027
Backyard-style ultra in Knoxville MD with repeating 4.167 mile laps every hour until one remains, plus a concurrent 1 mile Mortals edition.